Sinatra experienced a career crisis in the late 1940s, which coincided with the beginning of his romance to actress Ava Gardner.They married in 1951, but separated a few years later and divorced in 1957.

Mia Farrow

In 1966, Sinatra married the diminutive actress Mia Farrow, when he was 51 and she was 21. The marriage din't last long, and the couple divorced a little over a year later, in 1967.

Barbara Max

In 1976 Sinatra married Barbara Marx, the former wife of Zeppo Marx, who remained his wife the whole life long.